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Title: Nitroxyl-mediated oxidation of lignin and polycarboxylated products

Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on .beta.-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric .beta.-hydroxy acid. The polymeric .beta.-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The .beta.-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.
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Patent File Date: 2016 May 27
Research Org:
Chicago Operations Office, Argonne, IL (United States)
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Country of Publication:
United States

Other works cited in this record:

Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin
journal, April 2013
  • Rahimi, Alireza; Azarpira, Ali; Kim, Hoon
  • Journal of the American Chemical Society, Vol. 135, Issue 17, p. 6415-6418
  • DOI: 10.1021/ja401793n

Lignin Biosynthesis
journal, June 2003

Theory of Stationary Electrode Polarography. Single Scan and Cyclic Methods Applied to Reversible, Irreversible, and Kinetic Systems.
journal, April 1964
  • Nicholson, R. S.; Shain, Irving
  • Analytical Chemistry, Vol. 36, Issue 4, p. 706-723
  • DOI: 10.1021/ac60210a007

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010
  • Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L.
  • Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599
  • DOI: 10.1021/cr900354u

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